1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 178501159, compound

HRID 16717

Reaction equation

HRID 16717 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)=[O:4].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:36][N:37]([CH3:42])[CH2:38][CH2:39][NH:40][CH3:41].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:36][N:37]([CH3:42])[CH2:38][CH2:39][N:40]([CH3:41])[C:11]([C@H:8]1[CH2:7][CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]1)=[O:13]

Participants

7

Reactant 5

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178501163HCID 178501163, compound

Product 1

HCID 178501159HCID 178501159, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (8.84 g) obtained in Reference Example 1(2) is dissolved in chloroform (100 ml), and thereto are added 1-hydroxybenzotriazole (7.14 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (10.00 g) and N,N,N′-trimethylethylenediamine (5.33 g) under ice-cooling. The mixture is then stirred at room temperature for 4 hours. Saturated aqueous sodium hydrogen carbonate solution is poured to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with saturated brine and dried over sodium sulfate. The solvent is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol/28% ammonia water=200/10/1) to give methyl trans-4-{[[2-(dimethylamino)ethyl](methyl)amino]carbonyl}-cyclohexanecarboxylate (11.98 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solvent is concentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol/28% ammonia water=200/10/1)

Sources & evidence

ORD record
ord-8b58af24ecdb470eb2de945d1ee82651
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Linked notes

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